Hydrochloric Acid → 2-[4-(5-Dimethylamino-naphthalene-1-sulfonyl)-piperazin-1-yl]-thiazole-5-carboxylic acid hydroxyamide

HRID 1392953

反応式

HRID 1392953 の反応式
CO[C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[C:28]4[C:23](=[C:24]([N:29]([CH3:31])[CH3:30])[CH:25]=[CH:26][CH:27]=4)[CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][CH2:11]2)=[N:7][CH:6]=1)=[O:4].Cl.[NH2:33][OH:34].C[O-].[Na+].CO.Cl>O1CCOCC1>[OH:34][NH:33][C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[C:28]4[C:23](=[C:24]([N:29]([CH3:30])[CH3:31])[CH:25]=[CH:26][CH:27]=4)[CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][CH2:11]2)=[N:7][CH:6]=1)=[O:4]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 691997234-(5-Dimethylamino-naphthalene-1-sulfonyl)-piperazin-1-yl-thiazole-5-carboxylic acid methyl ester

生成物 1

HCID 111554392-[4-(5-Dimethylamino-naphthalene-1-sulfonyl)-piperazin-1-yl]-thiazole-5-carboxylic acid hydroxyamide収率 8%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a solution of compound (12k) (125 mg, 0.270 mmol) in 1,4-dioxane (2 mL) were added hydroxylamine hydrochloride (187 mg, 2.70 mmol) and a freshly prepared solution of sodium methoxide in methanol (92 mg, 4.00 mmol of sodium dissolved in 1 mL of methanol) under a N2 atmosphere. The reaction mixture was stirred at room temperature for 2 h (progress of the reaction was monitored by TLC analysis). The reaction mixture was acidified to pH˜6 with 1M HCl and the formed precipitates were filtered off. The filtrate was diluted with ethyl acetate (5 mL) and water (2 mL) and the organic layer was separated. The aqueous layer was washed with ethyl acetate (5 mL) and the combined organic layers were dried on sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC to give 13k (10 mg, yield 8.0%). HPLC: 90.69% (Rt=12.77 min).

後処理

  1. customthe formed precipitates
  2. filtrationwere filtered off
  3. additionThe filtrate was diluted with ethyl acetate (5 mL) and water (2 mL)
  4. customthe organic layer was separated
  5. washThe aqueous layer was washed with ethyl acetate (5 mL)
  6. customthe combined organic layers were dried on sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-ed097858cb66406d8f9d0b7f7ceaed99
出典データセット
uspto-grants-2008_03
特許番号
US07345043B2

関連ノート

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